Dimethyl Sulfoxide → HCID 12073625, compound

HRID 561766Notes

Reaction equation

HRID 561766 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C@H:12]1[CH2:16][C@H:15]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C@H:14]([CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[C@H:13]1[CH2:36][OH:37].OS([O-])(=O)=O.[K+]>C(Cl)Cl.C(N(CC)CC)C>[F:11][C@H:12]1[CH2:16][C@H:15]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C@H:14]([CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[C@H:13]1[CH:36]=[O:37]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 12073624HCID 12073624, compound

Product 1

HCID 12073625HCID 12073625, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (25 mL, 50 mmol) was dissolved in DCM (400 mL) and cooled to −78° C. under a nitrogen atmosphere, to which a solution consisting of DMSO (4.5 mL) in DCM (150 mL) was added. The reaction mixture was stirred for 15 minutes at −78° C. and a solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-3-fluoro-2-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step F, 12.94 g, 33.36 mmol) in DCM was subsequently added slowly. The reaction mixture was stirred for 40 minutes and triethylamine (28 mL) was subsequently added. Stirring was continued as the reaction mixture was allowed to warm to room temperature for 2 hours, monitoring by TLC. The reaction was acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. After drying over sodium sulfate, filtration, and solvent removal under reduced pressure, the crude product was purified on silica gel, eluted with hexanes-ethyl acetate (85:15) to afford the title intermediate (10.31 g, 80%).

Workup

  1. additionwas added
  2. additionwas subsequently added slowly
  3. stirringThe reaction mixture was stirred for 40 minutes
  4. stirringStirring
  5. temperatureto warm to room temperature for 2 hours
  6. extractionextracted with DCM
  7. washthe organic layers were washed twice with brine
  8. dry with materialAfter drying over sodium sulfate, filtration, and solvent removal under reduced pressure
  9. customthe crude product was purified on silica gel
  10. washeluted with hexanes-ethyl acetate (85:15)

Sources & evidence

ORD record
ord-c39ee27986b44c0c9bc6ee1bf087ff59
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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